Tony Baker Explores Chicago’s Comedy Legacy on “You Don’t Know Chi” w/ Shermann “Dilla” Thomas [Video]

Acclaimed comedian and cultural commentator Tony Baker joins Chicago historian and storyteller Shermann “Dilla” Thomas for a powerful and entertaining episode of You Don’t Know Chi, diving deep into the rich comedic roots of Chicago—a city widely recognized as one of the birthplaces of modern comedy.

In this dynamic installment, Baker teams up with Dilla to explore the neighborhoods, stages, and stories that helped shape generations of comedic voices. From the historic South Side to iconic performance spaces like The Second City and Harold Washington Cultural Center, the episode highlights how Chicago’s culture, resilience, and raw authenticity have influenced some of the most celebrated names in entertainment.

Blending humor with history, Baker offers his signature perspective as he learns how Chicago’s unique environment cultivated talent that would go on to impact television, film, and stand-up comedy worldwide. Dilla, known for his deep knowledge of Chicago’s untold stories, guides the journey—connecting the dots between the city’s past and its ongoing influence on the comedic landscape.

Throughout the episode, viewers are taken on a cultural tour of the city’s South Side neighborhoods, where community, struggle, and creativity intersect to fuel artistic expression. Together, Baker and Dilla uncover how Chicago’s grit and spirit became a training ground for comedic greatness, shaping voices that resonate far beyond the city limits.

You Don’t Know Chi continues its mission of spotlighting Chicago’s cultural impact through engaging storytelling and authentic perspectives. This episode stands as a testament to the city’s enduring legacy in comedy—and the voices that continue to carry it forward.

The episode featuring Tony Baker is now available for streaming on YouTube.